Quinacridone disperse yellow dyes with high sublimation fastness and a method for their synthesis

Abstract

This invention discloses a class of quinalidine disperse yellow dyes with high sublimation fastness and their synthesis method, belonging to the field of disperse dye technology. This invention uses Disperse Yellow 54 as the parent core and introduces one of the following substituents at the 6-position of the quinalidine ring: ethyl, n-propyl, cyclopropyl, cyclobutyl, cyclopropylmethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, cyclopropoxy, cyclobutoxy, cyclopropylmethoxy, 2-methoxyethoxy, fluorine, chlorine, bromine, cyano, or nitro. This invention uses 6-substituted-2-methyl-3-hydroxyquinoline-4-carboxylic acid and phthalic anhydride as raw materials, and synthesizes the target dye in one step via a high-temperature condensation reaction. Experimental results show that the sublimation fastness of the dye of this invention reaches grade 4-5 or 5, significantly improved compared to Disperse Yellow 54 (grade 2-3), while maintaining excellent resistance to rubbing, perspiration, and sunlight. This invention has a simple synthesis process, high yield, and high purity, possessing extremely high industrial production value and market application prospects.

Description

Technical Field

[0001] This invention belongs to the field of disperse dye technology, specifically relating to a class of quinalidine disperse yellow dyes with high sublimation fastness and their synthesis method. Background Technology

[0002] Disperse Yellow 54 (CI Disperse Yellow 54), chemically named 2-(3-hydroxyquinoline-2-yl)-indene-1,3-dione, is a class of yellow disperse dyes with a typical heterocyclic structure. Due to its bright color, high color strength, excellent lightfastness, good wash fastness, and good color matching compatibility, this dye is one of the best-performing yellow disperse dyes on the market and is widely used in the dyeing and printing processes of synthetic materials such as polyester fibers and polyester blended fibers.

[0003] However, Disperse Yellow 54 suffers from a long-standing technical shortcoming in practical applications—insufficient sublimation fastness. During finishing processes such as high-temperature setting, hot-melt dyeing, and heat transfer printing, as well as subsequent high-temperature ironing and drying, Disperse Yellow 54 molecules are prone to sublimation migration due to heat, leading to phenomena such as color fading, discoloration, and staining in dyed fabrics. This severely affects the appearance quality, color fastness stability, and lifespan of textiles. This problem is particularly prominent in high-end textile fabrics, automotive interiors, and outdoor textiles, where high-temperature processing stability and color fastness durability are crucial, and has become a major technical bottleneck restricting the widespread application of Disperse Yellow 54 in high-end fields.

[0004] To address the aforementioned issues, existing technologies have attempted to improve the sublimation fastness of Disperse Yellow 54 through physical blending, the addition of auxiliaries, or post-treatment modification. However, the effects are limited, and these methods often come at the cost of sacrificing other dyeing properties, making it difficult to achieve a balanced improvement in overall performance. Therefore, developing a novel yellow disperse dye with intrinsically high sublimation fastness at the molecular structure level, while maintaining the original excellent properties of Disperse Yellow 54, has become a pressing technical challenge in this field. Summary of the Invention

[0005] In view of this, the present invention aims to provide a class of quinalidine disperse yellow dyes with high sublimation fastness and a method for synthesizing the same.

[0006] To achieve the above objectives, the present invention provides the following technical solution:

[0007] This invention provides a class of quinalidine disperse yellow dyes with high sublimation fastness, characterized by the following structural formula: ; Where R is: One of the following: CH2CH3, (CH2)2CH3, cyclo-C3H5, cyclo-C4H7, CH2-cyclo-C3H5, OCH3, OCH2CH3, O(CH2)2CH3, OCH(CH3)2, O(CH2)3CH3, O-cyclo-C3H5, O-cyclo-C4H7, OCH2-cyclo-C3H5, O(CH2)2OCH3, F, Cl, Br, CN, NO2.

[0008] Furthermore, the synthetic route for quinalidine disperse yellow dye with high sublimation fastness is as follows:

[0009] This invention also provides a method for synthesizing the above-mentioned quinalidine disperse yellow dye with high sublimation fastness, characterized by comprising the following steps: After heating and melting phthalic anhydride, compound 1 was added while stirring, and the temperature was increased to carry out the reaction. After the reaction was completed, the product was placed in an aqueous sodium carbonate solution to dissolve excess phthalic anhydride (the mass fraction of the aqueous sodium carbonate solution was 8 wt%, and the liquid-solid ratio of the aqueous sodium carbonate solution to the reaction product was 7 mL:1 g). The product was then filtered and washed to obtain the product.

[0010] Preferably, the structural formula of compound 1 is:

[0011] Where R is: One of the following: CH2CH3, (CH2)2CH3, cyclo-C3H5, cyclo-C4H7, CH2-cyclo-C3H5, OCH3, OCH2CH3, O(CH2)2CH3, OCH(CH3)2, O(CH2)3CH3, O-cyclo-C3H5, O-cyclo-C4H7, OCH2-cyclo-C3H5, O(CH2)2OCH3, F, Cl, Br, CN, NO2.

[0012] Preferably, the molar ratio of phthalic anhydride to compound 1 is 1.1:1.

[0013] Preferably, the heating temperature is 180-200℃.

[0014] Preferably, the reaction temperature is 220-230℃ and the reaction time is 2h.

[0015] Preferably, the sodium carbonate aqueous solution is a sodium carbonate aqueous solution with a mass fraction of 5%-10%.

[0016] Preferably, the liquid-to-solid ratio of the sodium carbonate aqueous solution to the reaction product is 5-8 mL:1 g.

[0017] It contains at least the following beneficial technical effects: This invention effectively enhances the binding force between dye molecules and fibers by introducing a specific substituent at the 6-position of the quinalidine ring in the core of Disperse Yellow 54, thus inhibiting the sublimation migration of dye molecules under high-temperature conditions. Experimental data (see Table 2) show that the sublimation fastness of all 19 compounds in this invention reaches grade 4-5 or higher. Among them, compounds 4 (Example 3), 5 (Example 4), 6 (Example X), 7 (Example 5), 10 (Example X), 11 (Example 8), 13 (Example 9), 14 (Example 10), 17 (Example X), 18 (Example 13), and 19 (Example 14) reach grade 5, while the control sample Disperse Yellow 54 only reaches grade 2-3. This improvement solves the technical problem of color migration that easily occurs in traditional Disperse Yellow 54 during high-temperature setting, hot melt dyeing, and other finishing processes, meeting the stringent requirements of high-end polyester fabrics for high-temperature processing stability.

[0018] The dye of this invention significantly improves sublimation fastness while maintaining the excellent dyeing properties of Disperse Yellow 54. It does not require the use of toxic or harmful solvents or catalysts, and the post-treatment only requires dissolving excess phthalic anhydride in sodium carbonate aqueous solution. The process is highly safe, energy-efficient, and produces less waste, which is in line with the development direction of green chemical industry.

[0019] The product yields of the 19 embodiments of the present invention were all between 79.5% and 92.1%, and the HPLC content was all between 97.6% and 98.8%. The yield was calculated as yield = actual product mass / theoretical product mass × 100%, indicating that the synthesis method has excellent stability and reproducibility and is suitable for industrial production.

[0020] The dye of this invention is suitable for dyeing and printing processes of synthetic fibers such as polyester fibers and polyester blended fibers. It is especially suitable for processing scenarios with high requirements for sublimation fastness, such as high temperature setting and hot melt dyeing. It can be widely used in high-end textile fabrics, automotive interiors, outdoor textiles and other fields, and has good economic benefits and market competitiveness. Detailed Implementation

[0021] Various exemplary embodiments of the present invention will now be described in detail. This detailed description should not be considered as a limitation of the present invention, but rather as a more detailed description of certain aspects, features, and embodiments of the present invention.

[0022] It should be understood that the terminology used in this invention is merely for describing particular embodiments and is not intended to limit the invention. Furthermore, with respect to numerical ranges in this invention, it should be understood that each intermediate value between the upper and lower limits of the range is also specifically disclosed. Every smaller range between any stated value or intermediate value within a stated range, and any other stated value or intermediate value within said range, is also included in this invention. The upper and lower limits of these smaller ranges may be independently included or excluded from the range.

[0023] Unless otherwise stated, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. While only preferred methods and materials have been described herein, any methods and materials similar or equivalent to those described herein may be used in the implementation or testing of this invention. All references to this specification are incorporated by way of citation to disclose and describe methods and / or materials associated with those references. In the event of any conflict with any incorporated reference, the content of this specification shall prevail.

[0024] Various modifications and variations can be made to the specific embodiments described in this specification without departing from the scope or spirit of the invention, as will be apparent to those skilled in the art. Other embodiments derived from this specification will also be obvious to those skilled in the art. This application specification and embodiments are merely exemplary.

[0025] The terms “include,” “including,” “have,” “contain,” etc., used in this article are all open-ended terms, meaning that they include but are not limited to.

[0026] Unless otherwise specified, "room temperature" and "normal temperature" in this invention refer to 25±2℃.

[0027] Unless otherwise specified, all raw materials or instruments used in the following embodiments of the present invention are commercially available.

[0028] Example 12: Synthesis of 2-(3-hydroxy-6-ethylquinoline-2-yl)-indene-1,3-dione 162.8 g (1.1 mol) of phthalic anhydride was added to a 2000 mL four-necked flask and heated to 190 °C. After complete melting, stirring was started, and 231.0 g (1.0 mol) of 2-methyl-3-hydroxy-6-ethylquinoline-4-carboxylic acid was slowly added. The reaction was maintained at 225 °C for 2 h. The product was then placed in an aqueous sodium carbonate solution to dissolve excess phthalic anhydride (the sodium carbonate solution had a mass fraction of 8 wt%, and the liquid-solid ratio of the sodium carbonate solution to the reaction product was 7 mL:1 g). The product was filtered and washed to obtain 270.7 g of product, with a yield of 85.4% and a purity of 98.5%.

[0029] The analytical results of the refined product are as follows: MS (m / z): 318 [M+H] + Elemental analysis C 20 H 15 NO3: Measured values: C 75.88; H 4.90; N 4.68; Calculated values: C 75.71; H 4.73; N 4.42.

[0030] Example 22: Synthesis of 2-(3-hydroxy-6-n-propylquinoline-2-yl)-indene-1,3-dione 162.8 g (1.1 mol) of phthalic anhydride was added to a 2000 mL four-necked flask and heated to 190 °C. After complete melting, stirring was started, and 245.0 g (1.0 mol) of 2-methyl-3-hydroxy-6-n-propylquinoline-4-carboxylic acid was slowly added. The reaction was maintained at 220 °C for 2 h. The product was then placed in an aqueous sodium carbonate solution to dissolve excess phthalic anhydride (the sodium carbonate solution had a mass fraction of 5 wt%, and the liquid-solid ratio of the sodium carbonate solution to the reaction product was 6 mL:1 g). The product was filtered and washed to obtain 290.3 g of product, with a yield of 87.7% and a purity of 98.8%.

[0031] The analytical results of the refined product are as follows: MS (m / z): 332 [M+H] + Elemental analysis C 21 H 17 NO3: Measured values: C 76.35; H 5.28; N 4.38; Calculated values: C 76.13; H 5.14; N 4.23.

[0032] Example 32: Synthesis of 2-(3-hydroxy-6-cyclobutylquinoline-2-yl)-indene-1,3-dione 162.8 g (1.1 mol) of phthalic anhydride was added to a 2000 mL four-necked flask and heated to 180 °C. After complete melting, stirring was started, and 257.0 g (1.0 mol) of 2-methyl-3-hydroxy-6-cyclobutylquinoline-4-carboxylic acid was slowly added. The reaction was maintained at 230 °C for 2 h. The product was then placed in an aqueous sodium carbonate solution to dissolve excess phthalic anhydride (the sodium carbonate solution had a mass fraction of 10 wt%, and the liquid-to-solid ratio of the sodium carbonate solution to the reaction product was 8 mL:1 g). The product was filtered and washed to obtain 299.8 g of product, with a yield of 87.4% and a purity of 98.4%.

[0033] The analytical results of the refined product are as follows: MS (m / z): 344 [M+H] + Elemental analysis C 22 H 17 NO3: Measured values: C 77.11; H 5.21; N 4.18; Calculated values: C 76.97; H 4.96; N 4.08.

[0034] Example 42: Synthesis of 2-(3-hydroxy-6-cyclopropylmethylquinoline-2-yl)-indene-1,3-dione 162.8 g (1.1 mol) of phthalic anhydride was added to a 2000 mL four-necked flask and heated to 200 °C. After complete melting, stirring was started, and 257.0 g (1.0 mol) of 2-methyl-3-hydroxy-6-cyclopropylmethylquinoline-4-carboxylic acid was slowly added. The reaction was maintained at 225 °C for 2 h. The product was then placed in an aqueous sodium carbonate solution to dissolve excess phthalic anhydride (the sodium carbonate solution had a mass fraction of 8 wt%, and the liquid-to-solid ratio of the sodium carbonate solution to the reaction product was 7 mL:1 g). The product was filtered and washed to obtain 303.9 g of product, with a yield of 88.6% and a purity of 98.3%.

[0035] The analytical results of the refined product are as follows: MS (m / z): 344 [M+H] + Elemental analysis C 22 H 17 NO3: Measured values: C 77.14; H 5.13; N 4.20; Calculated values: C 76.97; H 4.96; N 4.08.

[0036] Example 52: Synthesis of 2-(3-hydroxy-6-ethoxyquinoline-2-yl)-indene-1,3-dione 162.8 g (1.1 mol) of phthalic anhydride was added to a 2000 mL four-necked flask and heated to 190 °C. After complete melting, stirring was started, and 247.0 g (1.0 mol) of 2-methyl-3-hydroxy-6-ethoxyquinoline-4-carboxylic acid was slowly added. The reaction was maintained at 225 °C for 2 h. The product was then placed in an aqueous sodium carbonate solution to dissolve excess phthalic anhydride (the sodium carbonate solution had a mass fraction of 8 wt%, and the liquid-solid ratio of the sodium carbonate solution to the reaction product was 7 mL:1 g). The product was filtered and washed to obtain 290.0 g of product, with a yield of 87.1% and a purity of 98.7%.

[0037] The analytical results of the refined product are as follows: MS (m / z): 334 [M+H] + Elemental analysis C 20 H 15 NO4: Measured values: C 72.29; H 4.65; N 4.41; Calculated values: C 72.07; H 4.50; N 4.20.

[0038] Example 62: Synthesis of 2-(3-hydroxy-6-n-propoxyquinoline-2-yl)-indene-1,3-dione 162.8 g (1.1 mol) of phthalic anhydride was added to a 2000 mL four-necked flask and heated to 190 °C. After complete melting, stirring was started, and 261.0 g (1.0 mol) of 2-methyl-3-hydroxy-6-n-propoxyquinoline-4-carboxylic acid was slowly added. The reaction was maintained at 225 °C for 2 h. The product was then placed in an aqueous sodium carbonate solution to dissolve excess phthalic anhydride (the sodium carbonate solution had a mass fraction of 8 wt%, and the liquid-solid ratio of the sodium carbonate solution to the reaction product was 7 mL:1 g). The product was filtered and washed to obtain 309.9 g of product, with a yield of 89.3% and a purity of 97.6%.

[0039] The analytical results of the refined product are as follows: MS (m / z): 348 [M+H] + Elemental analysis C 21 H 17 NO4: Measured values: C 72.77; H 5.03; N 4.16; Calculated values: C 72.62; H 4.90; N 4.03.

[0040] Example 72: Synthesis of 2-(3-hydroxy-6-isopropoxyquinoline-2-yl)-indene-1,3-dione 162.8 g (1.1 mol) of phthalic anhydride was added to a 2000 mL four-necked flask and heated to 190 °C. After complete melting, stirring was started, and 261.0 g (1.0 mol) of 2-methyl-3-hydroxy-6-isopropoxyquinoline-4-carboxylic acid was slowly added. The reaction was maintained at 225 °C for 2 h. The product was then placed in an aqueous sodium carbonate solution to dissolve excess phthalic anhydride (the sodium carbonate solution had a mass fraction of 8 wt%, and the liquid-to-solid ratio of the sodium carbonate solution to the reaction product was 7 mL:1 g). The product was filtered and washed to obtain 302.6 g of product, with a yield of 87.2% and a purity of 98.7%.

[0041] The analytical results of the refined product are as follows: MS (m / z): 348 [M+H] + Elemental analysis C 21 H 17 NO4: Measured values: C 72.83; H 5.09; N 4.21; Calculated values: C 72.62; H 4.90; N 4.03.

[0042] Example 82: Synthesis of 2-(3-hydroxy-6-cyclopropoxyquinoline-2-yl)-indene-1,3-dione 162.8 g (1.1 mol) of phthalic anhydride was added to a 2000 mL four-necked flask and heated to 190 °C. After complete melting, stirring was started, and 259.0 g (1.0 mol) of 2-methyl-3-hydroxy-6-cyclopropoxyquinoline-4-carboxylic acid was slowly added. The reaction was maintained at 225 °C for 2 h. The product was then placed in an aqueous sodium carbonate solution to dissolve excess phthalic anhydride (the sodium carbonate solution had a mass fraction of 8 wt%, and the liquid-to-solid ratio of the sodium carbonate solution to the reaction product was 7 mL:1 g). The product was filtered and washed to obtain 297.7 g of product, with a yield of 86.3% and a purity of 98.1%.

[0043] The analytical results of the refined product are as follows: MS (m / z): 346 [M+H] + Elemental analysis C 21 H 15 NO4: Measured values: C 73.22; H 4.52; N 4.17; Calculated values: C 73.04; H 4.35; N 4.06.

[0044] Example 92: Synthesis of 1,3-(3-hydroxy-6-cyclopropylmethoxyquinoline-2-yl)-indene-1,3-dione 162.8 g (1.1 mol) of phthalic anhydride was added to a 2000 mL four-necked flask and heated to 190 °C. After complete melting, stirring was started, and 273.0 g (1.0 mol) of 2-methyl-3-hydroxy-6-cyclopropylmethoxyquinoline-4-carboxylic acid was slowly added. The reaction was maintained at 225 °C for 2 h. The product was then placed in an aqueous sodium carbonate solution to dissolve excess phthalic anhydride (the sodium carbonate solution had a mass fraction of 8 wt%, and the liquid-to-solid ratio of the sodium carbonate solution to the reaction product was 7 mL:1 g). The product was filtered and washed to obtain 300.8 g of product, with a yield of 83.8% and a purity of 98.5%.

[0045] The analytical results of the refined product are as follows: MS (m / z): 360 [M+H] + Elemental analysis C 22 H 17 NO4: Measured values: C 73.69; H 4.98; N 4.06; Calculated values: C 73.54; H 4.74; N 3.90.

[0046] Example 102: Synthesis of [3-hydroxy-6-(2-methoxyethoxy)quinoline-2-yl]-indene-1,3-dione 162.8 g (1.1 mol) of phthalic anhydride was added to a 2000 mL four-necked flask and heated to 190 °C. After complete melting, stirring was started, and 277.0 g (1.0 mol) of 2-methyl-3-hydroxy-6-(2-methoxyethoxy)quinoline-4-carboxylic acid was slowly added. The reaction was maintained at 225 °C for 2 h. The product was then placed in an aqueous sodium carbonate solution to dissolve excess phthalic anhydride (the sodium carbonate solution had a mass fraction of 8 wt%, and the liquid-to-solid ratio of the sodium carbonate solution to the reaction product was 7 mL:1 g). The product was filtered and washed to obtain 309.3 g of product, with a yield of 85.2% and a purity of 98.6%.

[0047] The analytical results of the refined product are as follows: MS (m / z): 364 [M+H] + Elemental analysis C 21 H 17 NO5: Measured values: C 69.54; H 4.84; N 3.98; Calculated values: C 69.42; H 4.68; N 3.86.

[0048] Example 112 Synthesis of 2-(3-hydroxy-6-fluoroquinoline-2-yl)-indene-1,3-dione 162.8 g (1.1 mol) of phthalic anhydride was added to a 2000 mL four-necked flask and heated to 190 °C. After complete melting, stirring was started, and 221.0 g (1.0 mol) of 2-methyl-3-hydroxy-6-fluoroquinoline-4-carboxylic acid was slowly added. The reaction was maintained at 225 °C for 2 h. The product was then placed in an aqueous sodium carbonate solution to dissolve excess phthalic anhydride (the sodium carbonate solution had a mass fraction of 8 wt%, and the liquid-solid ratio of the sodium carbonate solution to the reaction product was 7 mL:1 g). The product was filtered and washed to obtain 260.3 g of product, with a yield of 84.8% and a purity of 98.8%.

[0049] The analytical results of the refined product are as follows: MS (m / z): 308 [M+H] + Elemental analysis C 18 H 10 NO3F: Measured values: C 70.60; H 3.42; N 4.76; F 6.27; Calculated values: C 70.36; H 3.26; N 4.56; F 6.19.

[0050] Example 122: Synthesis of 2-(3-hydroxy-6-chloroquinoline-2-yl)-indene-1,3-dione 162.8 g (1.1 mol) of phthalic anhydride was added to a 2000 mL four-necked flask and heated to 190 °C. After complete melting, stirring was started, and 237.5 g (1.0 mol) of 2-methyl-3-hydroxy-6-chloroquinoline-4-carboxylic acid was slowly added. The reaction was maintained at 225 °C for 2 h. The product was then placed in an aqueous sodium carbonate solution to dissolve excess phthalic anhydride (the sodium carbonate solution had a mass fraction of 8 wt%, and the liquid-to-solid ratio of the sodium carbonate solution to the reaction product was 7 mL:1 g). The product was filtered and washed to obtain 268.2 g of product, with a yield of 82.9% and a purity of 98.6%.

[0051] The analytical results of the refined product are as follows: MS (m / z): 324 [M+H] + Elemental analysis C 18 H 10 NO3Cl: Measured values: C 66.65; H 3.22; N 4.47; Cl 11.13; Calculated values: C 66.77; H 3.09; N 4.33; Cl 10.97.

[0052] Example 132: Synthesis of 2-(3-hydroxy-6-cyanoquinoline-2-yl)-indene-1,3-dione 162.8 g (1.1 mol) of phthalic anhydride was added to a 2000 mL four-necked flask and heated to 190 °C. After complete melting, stirring was started, and 228.0 g (1.0 mol) of 2-methyl-3-hydroxy-6-cyanoquinoline-4-carboxylic acid was slowly added. The reaction was maintained at 225 °C for 2 h. The product was then placed in an aqueous sodium carbonate solution to dissolve excess phthalic anhydride (the sodium carbonate solution had a mass fraction of 8 wt%, and the liquid-solid ratio of the sodium carbonate solution to the reaction product was 7 mL:1 g). The product was filtered and washed to obtain 249.6 g of product, with a yield of 79.5% and a purity of 98.4%.

[0053] The analytical results of the refined product are as follows: MS (m / z): 315 [M+H] + Elemental analysis C 19 H 10 N2O3: Measured values: C 72.76; H 3.32; N 9.06; Calculated values: C 72.61; H 3.18; N 8.92.

[0054] Example 142 Synthesis of 2-(3-hydroxy-6-nitroquinoline-2-yl)-indene-1,3-dione 162.8 g (1.1 mol) of phthalic anhydride was added to a 2000 mL four-necked flask and heated to 190 °C. After complete melting, stirring was started, and 248.0 g (1.0 mol) of 2-methyl-3-hydroxy-6-nitroquinoline-4-carboxylic acid was slowly added. The reaction was maintained at 225 °C for 2 h. The product was then placed in an aqueous sodium carbonate solution to dissolve excess phthalic anhydride (the sodium carbonate solution had a mass fraction of 8 wt%, and the liquid-solid ratio of the sodium carbonate solution to the reaction product was 7 mL:1 g). The product was filtered and washed to obtain 307.6 g of product, with a yield of 92.1% and a purity of 97.7%.

[0055] The analytical results of the refined product are as follows: MS (m / z): 335 [M+H] + Elemental analysis C 18 H 10 N2O5: Measured values: C 64.83; H 3.12; N 8.51; Calculated values: C 64.67; H 2.99; N 8.38.

[0056] The preparation methods of Examples 15-19 are the same as those of Example 1, except that the substituents of Compound 1 are cyclopropyl, methoxy, n-butoxy, cyclobutoxy, and bromine, respectively.

[0057] The analysis results are as follows: Example 15: The substituent was cyclopropyl. The analytical results of the purified product are as follows: MS (m / z): 330 [M+H] + Elemental analysis C 21 H 15 NO3: Measured values: C 76.77; H 4.71; N 4.42; Calculated values: C 76.60; H 4.56; N 4.26.

[0058] Example 16: The substituent was methoxy. The analytical results of the purified product are as follows: MS (m / z): 320 [M+H] + Elemental analysis C 19 H 13 NO4: Measured values: C 71.65; H 4.29; N 4.52; Calculated values: C 71.47; H 4.08; N 4.39.

[0059] Example 17: The substituent was n-butoxy. The analytical results of the purified product are as follows: MS (m / z): 362 [M+H] + Elemental analysis C 22 H 19 NO4: Measured values: C 73.28; H 5.45; N 4.02; Calculated values: C 73.13; H 5.26; N 3.88.

[0060] Example 18: The substituent was cyclobutoxy. The analytical results of the purified product are as follows: MS (m / z): 360 [M+H] + Elemental analysis C 22 H 17 NO4: Measured values: C 73.71; H 4.92; N 4.09; Calculated values: C 73.54; H 4.74; N 3.90.

[0061] Example 19: The substituent was bromine. The analytical results of the purified product are as follows: MS (m / z): 369 [M+H] + Elemental analysis C 18 H 10 NO3Br: Measured values: C 58.91; H 2.85; N 3.96; Br 21.89; Calculated values: C 58.70; H 2.72; N 3.80; Br 21.74.

[0062] Table 1 shows the structural and synthetic data of the compounds in Examples 1-19, as well as the synthetic data of several other substituent products.

[0063] Table 1

[0064] Experimental Example 1 The dye filter cake of this invention is mixed with a dispersant at a mass ratio of 1:1.5, and then milled (milling time 2 hours, particle size 1 μm) to achieve a diffusion level of 4 or higher (GB / T 2394-2013 "Determination of Diffusion Properties of Disperse Dyes"). After drying, the finished dye product is prepared. The dyeing process is as follows: Dye solution preparation: Weigh 1g of the finished dye, disperse and dilute with water to 500mL, transfer 20mL of the dye solution and mix with 60mL of water, and adjust the pH to 5 with acetic acid; Dyeing process: Add 4g of polyester fabric, start heating at 70℃, raise the temperature to 130℃ within 30 minutes, maintain the temperature for dyeing for 45 minutes, cool to 90℃ and remove the fabric sample; Post-treatment: The fabric samples were subjected to reduction cleaning (2 g / L sodium hydrosulfite, 1 g / L sodium hydroxide, 80℃ for 15 min), washing, and drying; Performance testing: Tests were conducted according to national standards GB / T3920-2008 (fastness to rubbing), GB / T3922-2013 (fastness to perspiration), GB / T5718-1997 ("Color fastness to dry heat (sublimation)" for textiles) and GB / T8430-2013 (fastness to sunlight). The comparison standard was Disperse Yellow 54. The test results are shown in Table 2. Table 2: Dyeing properties of the compounds of this invention.

[0065] Under equivalent conditions, all compounds of this invention exhibit sublimation fastness of grade 4-5, with 12 compounds reaching grade 5, significantly superior to the control sample Disperse Yellow 54's grade 2-3. This solves the color migration problem in the high-temperature finishing process of traditional dyes and meets the processing requirements of high-end polyester fabrics. The rubbing fastness (grade 4-5 / 5), perspiration fastness (grade 4-5 / 5), and light fastness (grade 6-7 / 7) are comparable to or slightly improved with Disperse Yellow 54, with 8 compounds achieving a light fastness of grade 7, demonstrating stronger weather resistance and a longer service life for dyed fabrics. Overall, the sublimation fastness of the disperse dyes of this invention is significantly better than that of Disperse Yellow 54, while other fastness properties are comparable to or slightly better than Disperse Yellow 54, indicating a promising market prospect.

[0066] The above description is only a preferred embodiment of the present invention. It should be noted that those skilled in the art can make several improvements and modifications without departing from the principle of the present invention, and these improvements and modifications should also be considered within the scope of protection of the present invention.

Claims

1. A class of quinalidine disperse yellow dyes with high sublimation fastness, characterized in that, Its structural formula is: ； Where R is: One of the following: CH2CH3, (CH2)2CH3, cyclo-C3H5, cyclo-C4H7, CH2-cyclo-C3H5, OCH3, OCH2CH3, O(CH2)2CH3, OCH(CH3)2, O(CH2)3CH3, O-cyclo-C3H5, O-cyclo-C4H7, OCH2-cyclo-C3H5, O(CH2)2OCH3, F, Cl, Br, CN, NO2.

2. The method for synthesizing the quinalidine disperse yellow dye with high sublimation fastness according to claim 1, characterized in that, Includes the following steps: After heating and melting phthalic anhydride, compound 1 was added while stirring, and the temperature was increased to carry out the reaction. After the reaction was completed, the product was placed in an aqueous sodium carbonate solution to dissolve excess phthalic anhydride (the mass fraction of the aqueous sodium carbonate solution was 8 wt%, and the liquid-solid ratio of the aqueous sodium carbonate solution to the reaction product was 7 mL:1 g). The product was then filtered and washed to obtain the product.

3. The synthesis method according to claim 2, characterized in that, The structural formula of compound 1 is: Where R is: One of the following: CH2CH3, (CH2)2CH3, cyclo-C3H5, cyclo-C4H7, CH2-cyclo-C3H5, OCH3, OCH2CH3, O(CH2)2CH3, OCH(CH3)2, O(CH2)3CH3, O-cyclo-C3H5, O-cyclo-C4H7, OCH2-cyclo-C3H5, O(CH2)2OCH3, F, Cl, Br, CN, NO2.

4. The synthesis method according to claim 3, characterized in that, The molar ratio of phthalic anhydride to compound 1 is 1.1:

1.

5. The synthesis method according to claim 2, characterized in that, The heating temperature is 180-200℃.

6. The synthesis method according to claim 2, characterized in that, The reaction temperature is 220-230℃, and the reaction time is 2 hours.

7. The synthesis method according to claim 2, characterized in that, The sodium carbonate aqueous solution is a sodium carbonate aqueous solution with a mass fraction of 5%-10%.

8. The synthesis method according to claim 2, characterized in that, The liquid-to-solid ratio of sodium carbonate aqueous solution to the reaction product is 5-8 mL: 1 g.

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